Mapping key amino acid residues for the epimerase efficiency and stereospecificity of the sex pheromone biosynthetic short-chain dehydrogenases/reductases of Nasonia

URN to cite this document:

urn:nbn:de:bvb:355-epub-382951 Copy

DOI to cite this document:

10.5283/epub.38295 Copy

Semmelmann, Florian ; Hofferberth, John ; Ruther, Joachim ; Sterner, Reinhard

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Date of publication of this fulltext: 04 Feb 2019 10:42

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Details

Item type:	Article
Journal or Publication Title:	Scientific Reports
Publisher:	NATURE PUBLISHING GROUP
Place of Publication:	LONDON
Volume:	9
Number of Issue or Book Chapter:	330
Page Range:	pp. 1-7
Date:	23 January 2019
Institutions:	Biology, Preclinical Medicine > Institut für Zoologie Biology, Preclinical Medicine > Institut für Zoologie > Chemische Ökologie (Prof. Dr. Joachim Ruther) Biology, Preclinical Medicine > Institut für Biophysik und physikalische Biochemie Biology, Preclinical Medicine > Institut für Biophysik und physikalische Biochemie > Prof. Dr. Reinhard Sterner
Projects:	Open Access Publizieren (DFG)
Identification Number:	Value Type 10.1038/s41598-018-37200-7 DOI
Keywords:	UDP-GALACTOSE 4-EPIMERASE; EVOLUTION; PTEROMALIDAE; SPECIFICITY;
Dewey Decimal Classification:	500 Science > 570 Life sciences 500 Science > 590 Zoological sciences
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	Yes
Item ID:	38295

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Abstract

Males of the parasitic wasp genus Nasonia use blends of chiral hydroxylactones as sex pheromones to attract conspecific females. Whereas all Nasonia species use a mixture of (4R,5S)-5-hydroxy-4-decanolide (RS) and 4-methylquinazoline (MQ) as sex pheromones, Nasonia vitripennis evolved (4R, 5R)-5-hydroxy-4-decanolide (RR) as an extra sex pheromone component. We recently identified and functionally ...

Abstract

Males of the parasitic wasp genus Nasonia use blends of chiral hydroxylactones as sex pheromones to attract conspecific females. Whereas all Nasonia species use a mixture of (4R,5S)-5-hydroxy-4-decanolide (RS) and 4-methylquinazoline (MQ) as sex pheromones, Nasonia vitripennis evolved (4R, 5R)-5-hydroxy-4-decanolide (RR) as an extra sex pheromone component. We recently identified and functionally characterized three short-chain dehydrogenases/ reductases (SDRs) NV10127, NV10128, and NV10129 that are capable of catalyzing the epimerization of RS to RR via (4R)-5-oxo-4-decanolide (ODL) as intermediate. Despite their very high sequence identities of 88-98%, these proteins differ drastically in their ability to epimerize RS to RR and in their stereoselectivity when reducing ODL to RR/RS. Here, in order to unravel the sequence differences underlying these varying functional properties of NV1027, NV10128 and NV10129, we created chimeras of the three enzymes and monitored their catalytic activities in vitro. The results show that a few amino acid changes at the C-termini and active sites of Nasonia vitripennis SDRs lead to substantially altered RS to RR epimerization and ODLreduction activities. Thus, our study adds to the understanding of pheromone evolution by showing that subtle mutations in key biosynthetic enzymes can result in drastic effects on the composition of chemical signals.

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Metadata last modified: 23 Mar 2021 17:56

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